The 34-year-old has replaced Danny Wilson as Chesterfield manager and inherited the task of keeping the Spireites in League One.
Unlike Wilson however, Caldwell is taking over a Town side in the relegation zone with just 19 games left in the League One season.
So what are the priorities in his new role?
Here’s what his checklist might look like...
1: Keep Town up
The main, most obvious objective for Caldwell is to ensure that come 2pm on Sunday 30th April, there are four other clubs below Chesterfield in the League One table.
While a surge up the division would be lovely, at this point there won’t be many fans who would turn their noses up at staying in the league on the merit of goal difference.
Where do you start? Chesterfield have said the timing of Danny Wilson’s sacking was to allow any new man to make changes while the January transfer window was still open.
Caldwell will undoubtedly already have names in mind of players he’d like to bring in.
It’s not quite that simple though, this isn’t Wigan Athletic, this is a club with a one-in, one-out transfer policy and no ‘wiggle room’ as Wilson put it.
The exit of Gary Liddle frees up some of the wage budget and a central midfielder would be a big help for this Town side.
Other areas he might look at include left-back, with Dan Jones suffering injury set-back after set-back and the wings, where the Spireites have lacked consistency and service for the front men.
3: Prepare for departures
Caldwell’s job might be further complicated should there be more departures in January.
Ched Evans is the likeliest target for lower table Championship clubs and upper echelon League Out outfits in need of a goalscorer.
The club have expressed their wish to keep the striker and have exercised their option to extend his contract by a further year.
But if someone was to come in with the kind of ‘crazy money’ Ashley Carson has talked about, Caldwell will need a proven striker, pronto, to fill that gap.
Other possible exits could come for Gboly Ariyibi, previously wanted by Brentford before a disappointing winter period on the pitch, who is out of contract this summer, and noises have been made about Jay O’Shea.
Jon Nolan too has been linked with other clubs and Caldwell will have to be prepared to react and replace if there’s a late January flurry of activity.
4: Decide on the ‘18’
Caldwell will have to oversee the rebuilding of a Chesterfield squad that could look completely different by the time next season rolls around.
There are 18 players out of contract this summer and departures are inevitable.
The new boss has decisions to make on youngsters like Rai Simons, Jake Beesley, Derek Daly, Laurence Maguire and Curtis Morrison.
And veterans, including Ian Evatt, player-coach Ritchie Humphreys, Sylvan Ebanks-Blake, Angel Martinez and Dan Jones could be coming to the end of their Chesterfield playing careers.
5: Attack, attack, attack
No one really expects a new manager to come in and turn this Chesterfield squad into an all-out attacking free-scoring machine.
If results have be ground out and winners come off shins or backsides, no one will really mind, this season at least.
But one of the big factors in Danny Wilson’s downfall was the eventual turning of the Proact crowd against what they perceived as negative tactics.
Caretaker Ritchie Humphreys went for a slightly more attacking formation on Saturday and late in the game the Spireites were still creating chances instead of parking the bus and hoping to cling on to that one-goal lead – and fans responded.
What’s needed at the Proact isn’t so much an abandonment of the senses and defensive responsibilities in favour of a lust for goals, but a rejuvenation of the confidence of flair players.
And something needs to be done about the service to Ched Evans – he needs chances to score goals and his goals might just keep Town up.